Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

doi:10.5012/bkcs.2008.29.5.953

Cited by 10 publications

References 14 publications

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Fluorescence Sensing and Selective Binding of a Novel 4,4′‐Sulfonyldianiline‐Bridged Bis(β‐cyclodextrin) for Bile Salts

Zhao¹,

Yang²,

Shao³

et al. 2010

Helvetica Chimica Acta

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A novel 4,4'-sulfonyldianiline-bridged bis(b-cyclodextrin (CD)) 2 was synthesized, and its complex stability constants (K s ) for the 1 : 1 inclusion complexation with bile salts, i.e., cholate (CA), deoxycholate (DCA), glycocholate (GCA), and taurocholate (TCA) have been determined in phosphate buffer (pH 7.2) at 258 by fluorescence spectroscopy. The result indicated that 2 can act as efficient fluorescent sensor and display remarkable fluorescence enhancement upon addition of optically inert bile salts. Structures of the inclusion complexes between bile salts and 2 were elucidated by 2D-NMR experiments, indicating that the anionic tail group and the D ring of bile salts penetrate into one CD cavity of 2 from the wide opening deeply, while the phenyl moiety of the CD linker is partially self-included in the other CD cavity to form a host -linker -guest binding mode. As compared with native b-CD 1 upon complexation with bile salts, bis(b-CD) 2 enhances the binding ability and molecular selectivity. Typically, 2 gives the highest K s value of 26200 m À1 for the complexation with CA, which may be ascribed to the simultaneous contributions of hydrophobic, H-bond, and electrostatic interactions. These phenomena are discussed from the viewpoints of multiple recognition and induce-fit interactions between host and guest.

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Fluorescence Sensing and Selective Binding of a Novel 4,4′‐Sulfonyldianiline‐Bridged Bis(β‐cyclodextrin) for Bile Salts

Zhao¹,

Yang²,

Shao³

et al. 2010

Helvetica Chimica Acta

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Synthesis of Novel Bis(β‐cyclodextrin)s Linked with Glycol and Their Inclusion Complexation with Organic Dyes

Zhao

Yang

Shi

et al. 2010

Helvetica Chimica Acta

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Three novel bis(b-cyclodextrin (CD))s with flexible glycol linkers, i.e., ethylene glycol-bridged bis(6-hydroxy-6-deoxy-b-CD) (2), diethylene glycol-bridged bis(6-hydroxy-6-deoxy-b-CD) (3), and triethylene glycol-bridged bis(6-hydroxy-6-deoxy-b-CD) (4) have been synthesized by the reaction of mono[6-O-(p-toluenesulfonyl)]-b-CD with corresponding materials. The inclusion complexation behaviors of these compounds 2 -4 with organic dyes; that is, acridine red (,3-trimethylphenazine-2,8-diamine hydrochloride; NR), ammonium 8-anilinonaphthalene-1-sulfonate (ANS), sodium 6-(p-toluidinyl)-naphthalene-2-sulfonate (TNS), rhodamine B (RhB) and brilliant green (¼ N-(4-{[4-(diethylamino)cyclohexa-2,5-dien-1-yl](phenyl)methyl}cyclohex-2-en-1-ylidene)-N-ethyl-ethanaminium hydrogen sulfate; BG), have been investigated at 258 in phosphate buffer (pH 7.20) by ultraviolet, fluorescence, and 2D-NMR spectroscopy. The results indicate that the two linked CD units may cooperatively bind a guest, and the molecular binding ability toward dye guests, especially bent ANS, T-shaped RhB, and triangular BG, can be extended. This cooperative binding mode is confirmed by Jobs experiments and 2D-NMR investigations. Furthermore, the complex stability depends greatly on the linker length of these glycol-bridged bis(b-CD)s and the size and shape of guest. The higher binding ability and selectivity of dye molecules by bis(b-CD)s 2 -4 are discussed from the viewpoint of size/shape-fit concept and multiple recognition mechanism.

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Todres

2013

Organic Chemistry in Confining Media

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Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

Cited by 10 publications

References 14 publications

Fluorescence Sensing and Selective Binding of a Novel 4,4′‐Sulfonyldianiline‐Bridged Bis(β‐cyclodextrin) for Bile Salts

Fluorescence Sensing and Selective Binding of a Novel 4,4′‐Sulfonyldianiline‐Bridged Bis(β‐cyclodextrin) for Bile Salts

Synthesis of Novel Bis(β‐cyclodextrin)s Linked with Glycol and Their Inclusion Complexation with Organic Dyes

Encapsulation Effects

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